CN102706980B - Method utilizing HPLC to test seventeen phenol substances contained in grapes and oranges - Google Patents
Method utilizing HPLC to test seventeen phenol substances contained in grapes and oranges Download PDFInfo
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Abstract
The invention discloses a method utilizing the HPLC (High Performance Liquid Chromatography) to test seventeen phenol substances contained in grapes and oranges, which comprises the following steps: firstly, separating the peel and pulp of the oranges or the grapes; secondly, drying and crushing the peel and pulp, and adding DMSO (Dimethyl Sulfoxide) : methanol (1:1) or a methanol solution into the peel and pulp to execute extraction; thirdly, after the collection of supernatant fluid, repeatedly extracting and compounding the supernatant fluid to execute HPLC detection; and lastly, identifying the sorts of the grapes and the oranges according to different sorts, content analysis of various phenol substances measured in different producing areas, and different chemical compound contents. The method disclosed by the invention adopts the HPLC to synchronously separate and test the seventeen phenol substances, and achieves the test to the ingredients and contents of the seventeen chemical compounds in different sorts of fruits such as the orange and the grapes and in wine, is simple in the pretreatment of the sample and low in cost, can synchronously test the ingredients and the contents of the phenol substances in the fruits, fruit juices and fruit wine.
Description
Technical field
The invention belongs to the analytical chemistry field, be specifically related to a kind of method that HPLC of utilization measures 17 kinds of aldehydes matters in grape and citrusfruit.
Background technology
Polyphenols comprises simple phenol and bioflavanoid.Simple phenols comprises that simple phenol and derivant thereof and simple phenolic acid class and derivant thereof are as caffeic acid, chlorogenic acid, gallic acid etc.Bioflavonoid can be divided into again two large compounds, and a class is the monomer of polyphenol, and non-polymer, comprise that various flavone compounds and glycoside thereof are as rutin, Quercetin, aurantiamarin, aurantiin, Nobiletin, hesperetin etc.; Another kind of is oligomer or the polymer formed by monomer polymerization.Aldehydes matter in fruit all has a great impact color and luster and the local flavor of fruit.Animal can not be synthesized flavonoids.Flavone compound extensively is present in fruit, and is distributed in plant the part of accepting sunlight more.The flavonoids material that human body is taken in approximately has 10% from fruit, and fruit is the good source of polyphenols.Grape and claret etc. are rich in resveratrol, and the resveratrol in grape berry mainly is distributed on pericarp.Strawberry, cherry, grape and oranges and tangerines etc. are rich in salicylic acid.Grape, the calyx and receptacle of a persimmon, pomegranate etc. contain gallic acid.Polyphenols has a certain amount of ROH base, can be formed with the hydroperoxyl radical (H) of antioxidation, to eliminate O
- 2with the activity of the free radical such as OH, thereby the protection body tissue is avoided the infringement of oxidation.That polyphenols has is anti-oxidant, strengthen immunologic function, anticancer, anti-ageing, regulate the biological actions such as capillary, antibiotic, anti-inflammatory, antiviral, hypotensive, reducing blood lipid, antithrombotic.
High performance liquid chromatography (HPLC) is widely used in a plurality of actual measurements fields such as residues of pesticides, hormone, polyphenols and organic acid because of validity and the accuracy of its detection.Generally, the side of utilizing high performance liquid chromatography to carry out sample regularly need to be passed through extraction and the purifying procedure of series of complex, and is detected under constant wavelength.For single-component system, it is effective under constant wavelength, measuring.But when multicomponent system is measured, because the maximum absorption wavelength of each component is not quite similar, loaded down with trivial details pretreatment process can make test substance that certain loss is arranged in addition, therefore utilizes the constant wave regular way to be difficult to the real content that complete detection goes out each component in multicomponent system.For the sensitivity that improves the multicomponent system detection the real content that reflects objectively tested component in polycomponent, should simplify as much as possible the pre-treatment step of sample and be detected under the maximum absorption wavelength of each material, especially to trace, trace materials.The main mensuration to 8 kinds of aldehydes matter contents such as gallic acid, protocatechuic acid, catechin, chlorogenic acid, epicatechin, caffeic acid, forulic acid or rutins in the patent of high-efficient liquid phase chromatogram process measuring method patent: Zhang Jinfen (CN200710045638.7) " a kind of method of simultaneously measuring multiple polyphenolic compound content of fruit ", and be characterised in that the fruit sample is apple skin, pears skin, banana skin, apple grunt or pears meat.The method of the patent (CN200710018742.7) " a kind of method with free phenol content in the Grape by HPLC tissue " of room Yulin etc. is mainly to gallic acid, protocatechuic acid, the 3-catechin, the 4-epicatechin, 5-epicatechin nutgall vinegar, 6 aldehydes matter contents such as 6-resveratrol are measured.Front 2 patents are mainly to concentrate on a few aldehydes matter to be measured, and mainly for be grape, apple and profit.Of the present invention mainly being intended to the gallic acid in oranges and tangerines and grape fruit, chlorogenic acid, caffeic acid, syringic acid, coumaric acid, rutin, forulic acid, sinapic acid, aurantiamarin, aurantiin, salicylic acid, Quercetin, Nobiletin, 17 kinds of aldehydes matters such as hesperetin (being mainly phenolic acid and flavones) carry out assay, and measurement range is wider.
The chemical qualitativity of polyphenol substance, quantitatively detect and isolation technics relates to several analytical approach use in conjunction such as stratographic analysis, spectral analysis, electrophoretic analysis, chemical analysis, instrumental analysis, sometimes also use sedimentation reaction.Adopt now the HPLC methods more.
Summary of the invention
The object of the present invention is to provide a kind of HPLC of utilization to measure the method for 17 kinds of aldehydes matters in grape and citrusfruit, according to different cultivars, the multiple aldehydes matter content analysis that the different places of production are surveyed, identified kind according to different compounds contents.The present invention adopts HPLC 17 kinds of aldehydes matters of separation determination simultaneously, and reaches the purpose to the identification of different cultivars oranges and tangerines, and the method sample pre-treatments is simple, cost is low, can measure simultaneously, realize the identification to different cultivars oranges and tangerines and grape, the identification of blended fruit juice Raw.
For achieving the above object, the present invention adopts following technical scheme:
A kind of method that HPLC of utilization measures 17 kinds of aldehydes matters in grape comprises the following steps:
(1) standard items: gallic acid, catechin, epicatechin, chlorogenic acid, caffeic acid, syringic acid, coumaric acid, rutin, forulic acid, benzoic acid, aurantiamarin, aurantiin, salicylic acid, Quercetin, resveratrol, Nobiletin, hesperetin are purchased from sigma company;
(2) sample pre-treatments
Take 2-3g freeze-dried fruit sample, add ethanol that massfraction is 50% to grind, be extracted with ethyl acetate 2 times, collect extract, be evaporated to dry, the mixed solution dissolving that the volume ratio that adds 2ml methyl alcohol and DMSO is 1:1;
(3) chromatographic condition
Chromatographic column Merck LiChrospher_100RP18e, 250mm * 4.0mm; Detect wavelength: 0-60min:230nm; 60-100min:280nm; Column temperature: 30 ℃; Gradient elution: mobile phase A Wei Shui ﹕ acetic acid=98 ﹕ 2; Mobile phase B is acetonitrile; Elution program: 0min → 100min, acetonitrile: 16% → 70%, 2% acetic acid water mixed liquid: 84% → 30%; Flow velocity: 0.8ml/min.
A kind of method that HPLC of utilization measures 17 kinds of aldehydes matters in citrusfruit comprises the following steps:
(1) standard items: gallic acid, catechin, epicatechin, chlorogenic acid, caffeic acid, syringic acid, coumaric acid, rutin, forulic acid, benzoic acid, aurantiamarin, aurantiin, salicylic acid, Quercetin, resveratrol, Nobiletin, hesperetin are purchased from sigma company;
(2) sample pre-treatments
First sample pulp is separated to freeze drying to cross 60 orders standby with pericarp; The mixed solution that to take the 0.1g sample be 1:1 by the volume ratio of 1mL methyl alcohol and DMSO is in soaking at room temperature 10min; 9000rpm, 4 ℃ of centrifugal 15min, repeat 3 times, merges supernatant in volumetric flask, uses methanol constant volume; Standby with 0.45 μ m filtering with microporous membrane;
(3) chromatographic condition
Chromatographic column Merck LiChrospher_100RP18e, 250mm * 4.0mm; Detect wavelength: 0-60min:230nm; 60-100min:280nm; Column temperature: 30 ℃; Gradient elution: mobile phase A Wei Shui ﹕ acetic acid=98 ﹕ 2; Mobile phase B is acetonitrile.Elution program: 0min → 100min, acetonitrile: 16% → 70%, 2% acetic acid water mixed liquid: 84% → 30%; Flow velocity: 0.8ml/min.
Remarkable advantage of the present invention is: according to different cultivars, the multiple aldehydes matter content analysis that the different places of production are surveyed, identified kind according to different compounds contents.The present invention utilizes HPLC to measure 17 kinds of aldehydes matters in grape and citrusfruit, and reaches the purpose to the identification of different cultivars oranges and tangerines, and the method sample pre-treatments is simple, cost is low, can measure simultaneously, realize the identification to different cultivars oranges and tangerines and grape, the identification of blended fruit juice Raw.
The accompanying drawing explanation
Fig. 1 is standard items HPLC collection of illustrative plates; 1-gallic acid wherein, 2-catechin, 3-chlorogenic acid, 4-caffeic acid, 5-syringic acid, 6-epicatechin, the 7-coumaric acid, 8-forulic acid, 9-benzoic acid, 10-salicylic acid, 11-rutin, 12-aurantiin, the 13-aurantiamarin, 14 resveratrols, 15-Quercetin, 16-Nobiletin, 17-hesperetin.
Fig. 2 is the standard items contour maps.
Embodiment
1 standard specimen: gallic acid, catechin, epicatechin, chlorogenic acid, caffeic acid, syringic acid, coumaric acid, rutin, forulic acid, benzoic acid, aurantiamarin, aurantiin, salicylic acid, Quercetin, resveratrol, Nobiletin, hesperetin are purchased from sigma company.
2 sample pre-treatments
Dry → 2ml dissolution with solvents (Jia Chun ﹕ DMSO=1 the ﹕ 1 of 2～3g freeze-dried fruit sample (wine) → 50% ethanol grinding → ethyl acetate extraction 2 times → collect extract → be evaporated to).
3 chromatographic conditions
Chromatographic column Merck LiChrospher_100RP18e (250mm * 4.0mm); Detect wavelength: 0-20min:230nm; 20-35min:280nm; 35-42min:309nm; 42-60min:320nm; Column temperature: 30 ℃; Gradient elution: mobile phase A Wei Shui ﹕ acetic acid=98 ﹕ 2; Mobile phase B is acetonitrile.Elution program: 0min → 100min, acetonitrile: 16% → 70%, 2% acetic acid water mixed liquid: 84% → 30%; Flow velocity: 0.8ml/min.
The content of aldehydes matter in table 1 grape fruit (μ g/g)
Embodiment 2 orange peel pulp
1 standard specimen: gallic acid, catechin, epicatechin, chlorogenic acid, caffeic acid, syringic acid, coumaric acid, rutin, forulic acid, benzoic acid, aurantiamarin, aurantiin, salicylic acid, Quercetin, resveratrol, Nobiletin, hesperetin are purchased from sigma company.
2 sample pre-treatments
First sample pulp is separated to freeze drying to cross 60 orders standby with pericarp; 0.1g sample mixes the 10min room temperature with 1mL methyl alcohol-DMSO (V/V.50:50), 9000rpm, and 4 ℃ of 15min are centrifugal, repeat 3 times, merge supernatant in volumetric flask, use methanol constant volume; Standby with 0.45 μ m filtering with microporous membrane.
3 chromatographic conditions
Chromatographic column Merck LiChrospher_100RP18e (250mm * 4.0mm); Detect wavelength: 0-20min:230nm; 20-35min:280nm; 35-42min:309nm; 42-60min:280nm; Column temperature: 30 ℃; Gradient elution: mobile phase A Wei Shui ﹕ acetic acid=98 ﹕ 2; Mobile phase B is acetonitrile.Elution program: 0min → 100min, acetonitrile: 16% → 70%, 2% acetic acid water mixed liquid: 84% → 30%; Flow velocity: 0.8ml/min.
The content of table 2 ponkan Phenolics In Fruit (μ g/g)
The extraction of aldehydes matter in embodiment 3 grape wine samples
1 standard specimen: gallic acid, catechin, epicatechin, chlorogenic acid, caffeic acid, syringic acid, coumaric acid, rutin, forulic acid, benzoic acid, aurantiamarin, aurantiin, salicylic acid, Quercetin, resveratrol, Nobiletin, hesperetin are purchased from sigma company.
2 sample pre-treatments
Free phenol in sampling and measuring grape wine, extracting method is similar to grape fruit, its process route: grape wine (10 ml) → 50% alcohol extract 2 times (5 times solid-liquid ratios, 70 ℃ extract 60 min) → reduced pressure concentration → chloroform extractions 2 times →
2 times → reduced pressure concentration → extract of ethyl acetate extraction → methyl alcohol dissolves, and is settled to 10 ml → 4 ℃ preservation, standby, repeats for 3 times.
3 chromatographic conditions
Chromatographic column Merck LiChrospher_100RP18e (250mm * 4.0mm); Detect wavelength: 0-20min:230nm; 20-35min:280nm; 35-42min:309nm; 42-60min:320nm; Column temperature: 30 ℃; Gradient elution: mobile phase A Wei Shui ﹕ acetic acid=98 ﹕ 2; Mobile phase B is acetonitrile.Elution program: 0min → 100min, acetonitrile: 16% → 70%, 2% acetic acid water mixed liquid: 84% → 30%; Flow velocity: 0.8ml/min.
The content of 17 kinds of aldehydes matters in table 3 grape wine
Detection limit and the recovery of the regression equation of 17 kinds of polyphenolic substances of table 4, related coefficient, the range of linearity, method
The foregoing is only preferred embodiment of the present invention, all equalizations of doing according to the present patent application the scope of the claims change and modify, and all should belong to covering scope of the present invention.
Claims (2)
1. a method of utilizing HPLC to measure 17 kinds of aldehydes matters in grape fruit, it is characterized in that: the assay method of grape phenols comprises the following steps:
(1) standard items: gallic acid, catechin, epicatechin, chlorogenic acid, caffeic acid, syringic acid, coumaric acid, rutin, forulic acid, benzoic acid, aurantiamarin, aurantiin, salicylic acid, Quercetin, resveratrol, Nobiletin, hesperetin are purchased from sigma company;
(2) sample pre-treatments
Take 2-3g freeze-dried fruit sample, add ethanol that massfraction is 50% to grind, be extracted with ethyl acetate 2 times, collect extract, be evaporated to dry, the mixed solution dissolving that the volume ratio that adds 2ml methyl alcohol and DMSO is 1:1;
(3) chromatographic condition
Chromatographic column Merck LiChrospher_100RP18e, 250mm * 4.0mm; Detect wavelength: 0-20min:230nm; 20-35min:280nm; 35-42min:309nm; 42-60min:320nm; Column temperature: 30 ℃; Gradient elution: mobile phase A Wei Shui ﹕ acetic acid=98 ﹕ 2; Mobile phase B is acetonitrile; Elution program: 0min → 100min, acetonitrile: 16% → 70%, 2% acetic acid water mixed liquid: 84% → 30%; Flow velocity: 0.8ml/min.
2. a method of utilizing HPLC to measure 17 kinds of aldehydes matters in citrusfruit, it is characterized in that: the assay method of orange peel pulp comprises the following steps:
(1) standard items: gallic acid, chlorogenic acid, caffeic acid, syringic acid, coumaric acid, rutin, forulic acid, aurantiamarin, aurantiin, salicylic acid, Quercetin, Nobiletin, hesperetin, catechin, epicatechin, benzoic acid, resveratrol are purchased from sigma company;
(2) sample pre-treatments
First sample pulp is separated to freeze drying to cross 60 orders standby with pericarp; The mixed solution that to take the 0.1g sample be 1:1 by the volume ratio of 1mL methyl alcohol and DMSO is in soaking at room temperature 10min; 9000rpm, 4 ℃ of centrifugal 15min, repeat 3 times, merges supernatant in volumetric flask, uses methanol constant volume; Standby with 0.45 μ m filtering with microporous membrane;
(3) chromatographic condition
Chromatographic column Merck LiChrospher_100RP18e, 250mm * 4.0mm; Detect wavelength: 0-20min:230nm; 20-35min:280nm; 35-42min:309nm; 42-60min:280nm; Column temperature: 30 ℃; Gradient elution: mobile phase A Wei Shui ﹕ acetic acid=98 ﹕ 2; Mobile phase B is acetonitrile; Elution program: 0min → 100min, acetonitrile: 16% → 70%, 2% acetic acid water mixed liquid: 84% → 30%; Flow velocity: 0.8ml/min.
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| CN103336069B (en) * | 2013-06-13 | 2015-06-10 | 江苏省农业科学院 | HPLC (High Performance Liquid Chromatography) determination method of phenolic compounds in peach fruit |
| CN104374854B (en) * | 2014-08-21 | 2016-03-09 | 中国食品发酵工业研究院 | A kind of method of multiple phenolic content in HPLC wavelength handoff technique Simultaneously test Noni juice |
| CN106153751A (en) * | 2015-04-13 | 2016-11-23 | 河北农业大学 | The efficient liquid-phase chromatography method of benzoic acid content in a kind of quick mensuration jujube fruit |
| CN105717227B (en) * | 2016-02-02 | 2017-08-04 | 天津科技大学 | A kind of concentrated apple juice flavor quality method of discrimination and its application |
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| CN105911173A (en) * | 2016-04-14 | 2016-08-31 | 梧州市产品质量检验所 | Determination method for chlorogenic acid in guiling jelly |
| CN107271581B (en) * | 2017-05-10 | 2019-04-19 | 四川农业大学 | A method of efficiently measuring phenolic compound in citrusfruit using HPLC |
| CN107917982B (en) * | 2017-11-09 | 2020-05-19 | 福建省农业科学院农业工程技术研究所 | Citrus variety identification and systematic classification method based on 21 characteristic component contents |
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| CN109187788A (en) * | 2018-09-21 | 2019-01-11 | 天津现代职业技术学院 | The measuring method of raw juice content in a kind of calcareous type orange drink |
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